DE862817C - Process for the preparation of water-soluble dyes of the phthalocyanine series - Google Patents
Process for the preparation of water-soluble dyes of the phthalocyanine seriesInfo
- Publication number
- DE862817C DE862817C DEB10070A DEB0010070A DE862817C DE 862817 C DE862817 C DE 862817C DE B10070 A DEB10070 A DE B10070A DE B0010070 A DEB0010070 A DE B0010070A DE 862817 C DE862817 C DE 862817C
- Authority
- DE
- Germany
- Prior art keywords
- water
- parts
- phthalocyanine
- soluble dyes
- tri
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000975 dye Substances 0.000 title claims description 13
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 150000003459 sulfonic acid esters Chemical class 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- 239000001045 blue dye Substances 0.000 description 4
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 229940008406 diethyl sulfate Drugs 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LQKAPWRNFKXLLV-UHFFFAOYSA-N N#CSC[Cu](CSC#N)(CSC#N)CSC#N Chemical compound N#CSC[Cu](CSC#N)(CSC#N)CSC#N LQKAPWRNFKXLLV-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical class CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- YPFNIPKMNMDDDB-UHFFFAOYSA-K 2-[2-[bis(carboxylatomethyl)amino]ethyl-(2-hydroxyethyl)amino]acetate;iron(3+) Chemical compound [Fe+3].OCCN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O YPFNIPKMNMDDDB-UHFFFAOYSA-K 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- KBIMRFLSIMMDOP-UHFFFAOYSA-N ClC[Co](CCl)CCl Chemical compound ClC[Co](CCl)CCl KBIMRFLSIMMDOP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- MPMSMUBQXQALQI-UHFFFAOYSA-N cobalt phthalocyanine Chemical compound [Co+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 MPMSMUBQXQALQI-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/32—Cationic phthalocyanine dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung wasserlöslicher Farbstoffe der Phthalocyaninreihe Es wurde gefunden, daB män wasserlösliche Farbstoffe der Phthalocyaninreihe erhält, wenn man wasserunlösliche Phthalocyanine, die ein- oder mehrmals über eine Schwefelbrücke eine Carboxyl- oder Thiocarlioxylgruppe oder einen diesen Gruppen entsprechenden funktionellen Abkömmling gebunden enthalten, mit Schwefelsäure- oder Sulfonsäureestern umsetzt.Process for the preparation of water-soluble dyes of the phthalocyanine series It has been found that water-soluble dyes of the phthalocyanine series can be obtained if you have water-insoluble phthalocyanines that cross a sulfur bridge one or more times a carboxyl or thiocarlioxyl group or one of these groups contain functional descendants bound with sulfuric acid or sulfonic acid esters implements.
Phthalocyanine der gekennzeichneten Art werden beispielsweise erhalten, wenn man diazotierte Aminophthalocyanine mit Xanthogenaten oder Rhodansalzen umsetzt oder wenn man halogenhaltige Phthalocyanine mit Salzen von Verbindungen der allgemeinen Formel H S -X, worin X eine Carboxyl- oder Thiocarboxylgruppe oder einen diesen Gruppen entsprechenden funktionellen Abkömmling bedeutet, umsetzt. Geeignete Verbindungen dieser Art sind beispielsweise Tri- oder Tetrathiocyanokupferphthalocyanin, Tri- oder Tetra-(äthylxanthogenato) -kupferphthalocyanin, Tetra- (thiocyanatomethyl) -kupferphthalocyanin, Di-, Tri-, Tetra- oder Penta-(äthyl- oder -butylxanthogenatomethyl)-kupferphthalocyanin, Gemische von Tri- und Tetra-(N, N-dimethyl- oder N, X-dibutyl- oder N, N-cyclotetramethylen- oder N-butyl-di-thiocarbamidomethyl)-kupferphthalocyanin oder die entsprechenden metallfreien oder kobalt-, eisen-, nickel- oder aluminiumhaltigen Phthalocyaninverbindungen. Als Ester der Schwefelsäure seien genannt: Dimethyl- oder Diäthylsülfat;:von den Estern der Sülfonsäuren kommen beispielsweise Benzol- oder Toluolsulfonsäureester in Betracht.Phthalocyanines of the type indicated are obtained, for example, when diazotized aminophthalocyanines are reacted with xanthates or rhodane salts or when halogen-containing phthalocyanines are reacted with salts of compounds of the general formula HS - X, in which X is a carboxyl or thiocarboxyl group or a functional derivative corresponding to these groups . Suitable compounds of this type are, for example, tri- or tetrathiocyanocopper phthalocyanine, tri- or tetra- (ethylxanthogenato) copper phthalocyanine, tetra- (thiocyanatomethyl) copper phthalocyanine, di-, tri-, tetra- or penta- (ethyl- or -butylxanthogenatomethyl) copper phthalocyanine , Mixtures of tri- and tetra- (N, N-dimethyl- or N, X-dibutyl- or N, N-cyclotetramethylene- or N-butyl-di-thiocarbamidomethyl) copper phthalocyanine or the corresponding metal-free or cobalt, iron , nickel- or aluminum-containing phthalocyanine compounds. The following may be mentioned as esters of sulfuric acid: dimethyl or diethyl sulphate: of the esters of sulphonic acids, for example benzene or toluenesulphonic acid esters are suitable.
Die Umsetzung erfolgt durch Erwärmen der genannten Phthalocyanine mit den Schwefel- oder Sulfonsäureestern, gegebenenfalls in Gegenwart indifferenter Lösungs- oder Verdünnungsmittel. Die neuen Erzeugnisse sind grüne bis blaue Farbstoffe, die zum Färben und Bedrucken von Textilien Verwendung finden. Die Färbungen sind gut wasch- und lichtecht.The reaction takes place by heating the phthalocyanines mentioned with the sulfuric or sulfonic acid esters, optionally in the presence of indifferent ones Solvents or thinners. The new products are green to blue dyes, which are used for dyeing and printing textiles. The colorations are well washable and lightfast.
Die in.folgenden Beispielen genannten Teile sind Gewichtsteile. Beispiel = Ein Gemisch aus 3o Teilen feingemahlenem Tetra-(thiocyanatomethyl)-kupferphthalocyanin, hergestellt aus Tetra-(halogenmethyl)-kupferphthalocyanin und Kaliumthiocyanat, und i2o Teilen Dimethylsulfat wird unter Rühren 8 bis 9 Stunden auf iio bis i2o° erhitzt. Nach dem Erkalten gibt man zu dem Gemisch igo Teile Aceton, Essigester oder Chloroform, saugt den ausgeschiedenen Niederschlag ab und trocknet ihn bei niedriger Temperatur. Man erhält einen wasserlöslichen Farbstoff, der beim Direkt-oder Reservedruck auf Baumwolle oder Acetatseide grünstichigblaue Drucke ergibt. Beispiel 2 In 125 Teile Diäthylsulfat werden 25 Teile gepulvertes Tetra-(thiocyanatomethyl)-kupferphthalocyanin eingerührt, und das Gemisch wird io Stunden auf ioo bis zio° erhitzt. Nach der Fällung mit Aceton erhält man 39 Teile eines wasserlöslichen Pulvers, das Baumwolle oder Acetatseide aus neutraler Lösung blau färbt. Beispiel 3 3o Teile Tri-(butylxanthogenatomethyl)-kobaltphthalocyanin, erhältlich aus Tri-(chlormethyl)-kobaltphthalocyanin, Schwefelkohlenstoff und Natriumbutylat, trägt man unter Rühren in ioo Teile Dimethylsulfat ein und erwärmt das Gemisch etwa i Stunde lang auf ioo°. Der auf Zusatz von Aceton ausgeschiedene Niederschlag wird abgesaugt und getrocknet. Der erhaltene blaue Farbstoff färbt Baumwolle aus neutralem Bad in blauen Tönen.The parts mentioned in the following examples are parts by weight. example = A mixture of 3o parts of finely ground tetra (thiocyanatomethyl) copper phthalocyanine, made from tetra (halomethyl) copper phthalocyanine and potassium thiocyanate, and i2o parts of dimethyl sulphate is stirred for 8 to 9 hours at 110 to 120 ° heated. After cooling, igo parts of acetone and ethyl acetate are added to the mixture or chloroform, sucks off the deposited precipitate and dries it low temperature. A water-soluble dye is obtained which, in the case of direct or Reserve print on cotton or acetate silk produces greenish blue prints. example 2 25 parts of powdered tetra (thiocyanatomethyl) copper phthalocyanine are added to 125 parts of diethyl sulfate stirred in, and the mixture is heated to 100 to 10 ° for 10 hours. After the felling with acetone 39 parts of a water-soluble powder, the cotton or Acetate silk dyes blue from a neutral solution. Example 3 3o parts of tri- (butylxanthogenatomethyl) cobalt phthalocyanine, available from tri- (chloromethyl) cobalt phthalocyanine, carbon disulfide and sodium butoxide, one carries in 100 parts of dimethyl sulfate with stirring and the mixture is warmed about ioo ° for i hour. The precipitate which separates out on the addition of acetone is vacuumed and dried. The blue dye obtained dyes cotton from neutral Bathroom in blue tones.
Ähnliche Farbstoffe erhält man aus Tri-(butylxanthogenatomethyl)-phthalocyanin oder- kupferphthalocyanin. _ Beispiel 4 e Ein Gemisch aus 5o Teilen p-Toluolsulfosäuremethylester und 5 Teilen Tri-(N, N-cyclotetramethylendithiocärbämidomethyl)-kupferphthalocyanin, erhalten aus Tri-(clilormethyl)-kupferphthalocyanin, Schwefelkohlenstoff und Pyrrolidin, wird etwa io Stunden unter Rühren auf i2o° erwärmt. Nach Zusatz von Aceton wird der ausgefallene Niederschlag abgesaugt,, gewaschen und getrocknet. Man erhält einen blauen Farbstoff, der Baumwolle aus amisensaurem Bad oder Acetatseide aus wäBrigem Bad in blauen Tönen färbt. Beispiel 5 Ein Gemisch aus io Teilen Tetra-(äthylxanthogenato)-kupferphthalocyanin, erhältlich durch Umsetzung - von Äthylxanthogenat mit diazotiertem Tetraaminokupferphthalocyanin, und 8o Teilen Dimethyl-oder Diäthylsulfatwird unter Rühren 8 Stunden lang auf iio° erhitzt. Nach der üblichen Aufarbeitung erhält man ein dunkelgrünes Pulver, das aus schwach ameisensaurer Lösung Acetatseide, Wolle oder Baumwolle in blaustichiggrünen Tönen färbt. Beispiel 6 Ein Gemisch aus 3o Teilen Tri-(N, N-cyclotetramethylendithiocarbamidomethyl) - kupferphthalocyanin und ioo Teilen Dimethylsulfat wird 4 bis 5 Stunden lang unter Rühren auf ioo° erhitzt. Nach der üblichen Aufarbeitung erhält man einen wasserlöslichen Farbstoff, der Baumwolle, Acetatseide oder Wolle aus neutraler Lösung blau färbt. Auch zum Bedrucken dieser Textilarten ist der Farbstoff brauchbar. Ebenfalls wasserlösliche blaue Farbstoffe werden erhalten, wenn man ein Gemisch von Tri- und Tetra-(N, N-dibutyl- oder N-butyldithiocarbamidomethyl)-kupferphthalocyanin oder Tri-(N, N-dimethyl- bzw. -diäthyldithiocarbamidomethyl)-kobaitphthalocyanin mit Dimethyl- oder Diäthylsulfat 'umsetzt.Similar dyes are obtained from tri- (butylxanthogenatomethyl) phthalocyanine or copper phthalocyanine. Example 4 e A mixture of 50 parts of p-toluenesulfonic acid methyl ester and 5 parts of tri- (N, N-cyclotetramethylenedithiocarbämidomethyl) copper phthalocyanine, obtained from tri- (clilomethyl) copper phthalocyanine, carbon disulfide and pyrrolidine, is heated to 120 ° for about 10 hours with stirring warmed up. After adding acetone, the precipitate is filtered off with suction, washed and dried. A blue dye is obtained which dyes cotton from an acidic bath or acetate silk from an aqueous bath in blue tones. EXAMPLE 5 A mixture of 10 parts of tetra (äthylxanthogenato) copper phthalocyanine, obtainable by reaction of ethyl xanthate with diazotized tetraamino copper phthalocyanine, and 80 parts of dimethyl or diethyl sulfate is heated to 10 ° for 8 hours with stirring. After the usual work-up, a dark green powder is obtained which, from a weakly formic acid solution, dyes acetate silk, wool or cotton in bluish green shades. Example 6 A mixture of 30 parts of tri- (N, N-cyclotetramethylene dithiocarbamidomethyl) copper phthalocyanine and 100 parts of dimethyl sulfate is heated to 100 ° for 4 to 5 hours with stirring. After the usual work-up, a water-soluble dye is obtained which dyes cotton, acetate silk or wool blue from a neutral solution. The dye can also be used for printing on these types of textile. Also water-soluble blue dyes are obtained if a mixture of tri- and tetra- (N, N-dibutyl- or N-butyldithiocarbamidomethyl) -copper phthalocyanine or tri- (N, N-dimethyl- or diethyldithiocarbamidomethyl) -kobaitphthalocyanine with dimethyl - or diethyl sulfate '.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB10070A DE862817C (en) | 1950-09-22 | 1950-09-23 | Process for the preparation of water-soluble dyes of the phthalocyanine series |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1041540X | 1950-09-22 | ||
| DEB10070A DE862817C (en) | 1950-09-22 | 1950-09-23 | Process for the preparation of water-soluble dyes of the phthalocyanine series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE862817C true DE862817C (en) | 1953-01-12 |
Family
ID=25964893
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB10070A Expired DE862817C (en) | 1950-09-22 | 1950-09-23 | Process for the preparation of water-soluble dyes of the phthalocyanine series |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE862817C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2855403A (en) * | 1956-02-16 | 1958-10-07 | American Cyanamid Co | Nonflocculating, noncrystallizing phthalocyanine pigments |
-
1950
- 1950-09-23 DE DEB10070A patent/DE862817C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2855403A (en) * | 1956-02-16 | 1958-10-07 | American Cyanamid Co | Nonflocculating, noncrystallizing phthalocyanine pigments |
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